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Originally Posted by healer
Confidence is definitely something that I find difficult to express when in new and different situations. Getting over the fear of rejection and embarrassment was the biggest hurdle for me.
Strangely, I've noticed a marked difference since I got married. Striking up a conversation with strangers or people that are only acquaintances has become alot easier - especially with the ladies. mandy says I'm turning into a flirt, and that I didn't get a chance to use my mojo in my youth so now it's leaking out.
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Rejection is a huge issue for some guys (gals as well I would guess). Some guys shake off getting turned down like taking another breath, for others it's like a punch in the gut.
I was a late bloomer, didn't gain any real confidence until my late 20s, after I had been married a few years. Marriage helped me to figure out that women were willing to overlook flaws. Also, in my limited experience, our (male & female) expectations change as we grow older.
One place where I never had any luck with women was at bars. It seemed to me, at the time, that there was way too much competition (possibly true); I anticipated getting turned down before I ever opened my mouth. I was much more relaxed when talking to women at the library, coffee shop, etc.
As others have said...
Practice talking to women. It might help to do so outside of the bar scene. Believe it or not, women will be understanding if you don't always have something clever or interesting to say. Learn to ask questions and learn to listen. Don't be overly worried about gaps in the conversation, chances are she is also trying to think of something interesting to say, & doesn't expect you to carry the conversation. Sometimes sharing a few minutes of silence actually helps you and the woman relax.
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A digression--I worked with a young man in his early 20s who was good-looking, intelligent, well-spoken, took pride in his appearnace, had a great physique, impeccable manners, and was a genuinely nice guy. But he was
painfully introverted. A few months after he got married he began to figure out women don't bite, & he rapidlyo developed a lot of self-confidence (which was a good thing). The down side was he started to recognize when women were hitting on him, and thoroughly enjoyed the attention & the flirting. It reached the point where I, and the older woman in our small office, warned him that he was walking on thin ice.